Tough choice for #1. I haven't driven too many cool/fast cars.
#1-My dad'* 1970 Corvette (350 V8 )-It'* fast, light and low so it handles nicer than my car.
#2-My 1968 Cutlass (455 V8 )-Lots of torque, but not a cornering machine.
#3-My mom'* former red 1967 Mustang convertible that was traded in for my dad'* Vette (289 V8 )-just a fun little car with some decent power.
#4-My neighbor'* 1969 Pontiac Tempest (350 V8 )-Recently rebuilt and overbored, also had positraction put in. Manual brakes though.
#5-Nothing else particularly cool so I'll put my dad'* 1930 Model A sedan. That was the first car I drove in our back yard when I was like 12. It was a stick so it was very tough to learn. I drove it a few times when I was older and it was fun to putz around in.